JPH0433440B2 - - Google Patents
Info
- Publication number
- JPH0433440B2 JPH0433440B2 JP57223112A JP22311282A JPH0433440B2 JP H0433440 B2 JPH0433440 B2 JP H0433440B2 JP 57223112 A JP57223112 A JP 57223112A JP 22311282 A JP22311282 A JP 22311282A JP H0433440 B2 JPH0433440 B2 JP H0433440B2
- Authority
- JP
- Japan
- Prior art keywords
- extraction solvent
- broth
- avermectin
- extraction
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000605 extraction Methods 0.000 claims abstract description 47
- 239000002904 solvent Substances 0.000 claims abstract description 46
- 239000005660 Abamectin Substances 0.000 claims abstract description 33
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims abstract description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 5
- 238000000855 fermentation Methods 0.000 claims description 5
- 230000004151 fermentation Effects 0.000 claims description 5
- 239000002699 waste material Substances 0.000 claims description 5
- 239000003518 caustics Substances 0.000 claims description 4
- 238000010908 decantation Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 7
- 238000002425 crystallisation Methods 0.000 abstract description 3
- 230000008025 crystallization Effects 0.000 abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 3
- 239000011707 mineral Substances 0.000 abstract description 3
- 235000010633 broth Nutrition 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000012546 transfer Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
- C12P19/623—Avermectin; Milbemycin; Ivermectin; C-076
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Feed For Specific Animals (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/332,418 US4423211A (en) | 1981-12-21 | 1981-12-21 | Process for the whole broth extraction of avermectin |
| US332418 | 1981-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58170490A JPS58170490A (ja) | 1983-10-07 |
| JPH0433440B2 true JPH0433440B2 (enrdf_load_stackoverflow) | 1992-06-03 |
Family
ID=23298145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57223112A Granted JPS58170490A (ja) | 1981-12-21 | 1982-12-21 | アベルメクチンの全ブロス抽出法 |
Country Status (10)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5077398A (en) * | 1986-11-18 | 1991-12-31 | Merck & Co., Inc. | Process for isolation of avermectin B1 components with improved purity and subsequent isolaton of B2 components |
| IT1255135B (it) * | 1992-05-05 | 1995-10-20 | Principio attivo a base di avermectine, ceppo e procedimento per la sua preparazione e composizione veterinaria che lo contiene. | |
| KR100419554B1 (ko) * | 1999-10-29 | 2004-02-19 | 주식회사유한양행 | 아버멕틴의 정제방법 |
| US6573074B2 (en) * | 2000-04-12 | 2003-06-03 | Smithkline Beecham Plc | Methods for ansamitocin production |
| DE102004032659B4 (de) * | 2004-07-01 | 2008-10-30 | Atotech Deutschland Gmbh | Vorrichtung und Verfahren zum chemischen oder elektrolytischen Behandeln von Behandlungsgut sowie die Verwendung der Vorrichtung |
| CN102217591A (zh) * | 2011-04-26 | 2011-10-19 | 张福志 | 一种环保型阿维菌素油膏生产工艺 |
| CN102977168B (zh) * | 2012-12-17 | 2013-08-21 | 石家庄市兴柏生物工程有限公司 | 一种阿维菌素B2a的提取制备方法 |
| EP2886640A1 (en) | 2013-12-18 | 2015-06-24 | Riga Technical University | Process for isolation of milbemycins A3 and A4 |
| CN105001287B (zh) * | 2015-06-30 | 2018-03-13 | 芜湖福民生物药业有限公司 | 阿维菌素的制备方法 |
| CN105503982A (zh) * | 2015-11-17 | 2016-04-20 | 石家庄市兴柏生物工程有限公司 | 一种阿维菌素提取工艺 |
| CN115873050B (zh) * | 2021-09-28 | 2024-11-08 | 浙江珲达生物科技有限公司 | 一种伊维菌素的制备方法 |
| CN116284182B (zh) * | 2021-12-21 | 2024-10-25 | 宁夏泰益欣生物科技股份有限公司 | 一种利用微波及溶剂回流技术提取阿维菌素的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1422031A (fr) * | 1963-12-17 | 1965-12-24 | Bristol Banyu Res Inst | Préparation d'un nouvel antibiotique à partir de streptomyces |
| US4062948A (en) * | 1970-08-14 | 1977-12-13 | Gist-Brocades N.V. | Dihydromocimycin antibiotics |
| SE434277B (sv) * | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
| US4161583A (en) * | 1977-10-03 | 1979-07-17 | Merck & Co., Inc. | Method for the separation and purification of antibiotic macrolides |
| US4172940A (en) * | 1977-10-03 | 1979-10-30 | Merck & Co., Inc. | Purification of C-076 compounds by single column chromatography |
| US4160083A (en) * | 1977-10-03 | 1979-07-03 | Merck & Co., Inc. | Process for the separation of antibiotic macrolides |
| US4160861A (en) * | 1977-10-03 | 1979-07-10 | Merck & Co., Inc. | Method for the separation of antibiotic macrolides |
| US4199569A (en) * | 1977-10-03 | 1980-04-22 | Merck & Co., Inc. | Selective hydrogenation products of C-076 compounds and derivatives thereof |
| US4160084A (en) * | 1977-10-11 | 1979-07-03 | Merck & Co., Inc. | Method for the separation of antibiotic macrolides |
| US4285963A (en) * | 1980-08-07 | 1981-08-25 | Merck & Co., Inc. | Novel derivatives of C-076 compounds |
-
1981
- 1981-12-21 US US06/332,418 patent/US4423211A/en not_active Expired - Lifetime
-
1982
- 1982-12-06 CA CA000417033A patent/CA1185198A/en not_active Expired
- 1982-12-15 DE DE8282306704T patent/DE3267718D1/de not_active Expired
- 1982-12-15 AT AT82306704T patent/ATE16707T1/de not_active IP Right Cessation
- 1982-12-15 EP EP82306704A patent/EP0082674B1/en not_active Expired
- 1982-12-16 GR GR70095A patent/GR77812B/el unknown
- 1982-12-20 PT PT76002A patent/PT76002B/pt unknown
- 1982-12-20 ES ES518358A patent/ES8402345A1/es not_active Expired
- 1982-12-20 DK DK562282A patent/DK562282A/da not_active Application Discontinuation
- 1982-12-21 JP JP57223112A patent/JPS58170490A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0082674A2 (en) | 1983-06-29 |
| ES518358A0 (es) | 1984-02-01 |
| JPS58170490A (ja) | 1983-10-07 |
| PT76002B (en) | 1985-12-13 |
| ATE16707T1 (de) | 1985-12-15 |
| ES8402345A1 (es) | 1984-02-01 |
| CA1185198A (en) | 1985-04-09 |
| GR77812B (enrdf_load_stackoverflow) | 1984-09-25 |
| DK562282A (da) | 1983-06-22 |
| EP0082674A3 (en) | 1983-07-27 |
| US4423211A (en) | 1983-12-27 |
| EP0082674B1 (en) | 1985-11-27 |
| DE3267718D1 (en) | 1986-01-09 |
| PT76002A (en) | 1983-01-01 |
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